EP0463877A1 - Préparation pharmaceutique à libération contrôlée - Google Patents

Préparation pharmaceutique à libération contrôlée Download PDF

Info

Publication number
EP0463877A1
EP0463877A1 EP91305834A EP91305834A EP0463877A1 EP 0463877 A1 EP0463877 A1 EP 0463877A1 EP 91305834 A EP91305834 A EP 91305834A EP 91305834 A EP91305834 A EP 91305834A EP 0463877 A1 EP0463877 A1 EP 0463877A1
Authority
EP
European Patent Office
Prior art keywords
water
pharmaceutical preparation
coating layer
controlled release
acrylic polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP91305834A
Other languages
German (de)
English (en)
Other versions
EP0463877B2 (fr
EP0463877B1 (fr
Inventor
Kazuo Noda
Takashi Osawa
Masao Kobayashi
Shigeyuki Ishikawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tanabe Seiyaku Co Ltd
Original Assignee
Tanabe Seiyaku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26494375&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0463877(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Tanabe Seiyaku Co Ltd filed Critical Tanabe Seiyaku Co Ltd
Publication of EP0463877A1 publication Critical patent/EP0463877A1/fr
Application granted granted Critical
Publication of EP0463877B1 publication Critical patent/EP0463877B1/fr
Publication of EP0463877B2 publication Critical patent/EP0463877B2/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
    • A61K9/2846—Poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core

Definitions

  • the present invention relates to a controlled release pharmaceutical preparation, and more particularly to a so-called sigmoid type controlled release pharmaceutical preparation (Sigmoidal-Releasing System) from which a medicinal compound rapidly dissolves after a certain lag time.
  • sigmoid type controlled release pharmaceutical preparation Sigmoidal-Releasing System
  • a sustained release pharmaceutical preparation in which a core is alterately coated with two compositions, namely, with a coating composition comprising a water-soluble polymer such as a polyvinyl alcohol or polyvinylpyrrolidone and a water-insoluble polymer such as ethylcellulose, polyvinyl chloride or Eudragit RS (trade mark, from Röhm Pharma, Germany), and a composition comprising diltiazem hydrochloride, an organic acid and a lubricant to form multi coating layers.
  • a coating composition comprising a water-soluble polymer such as a polyvinyl alcohol or polyvinylpyrrolidone and a water-insoluble polymer such as ethylcellulose, polyvinyl chloride or Eudragit RS (trade mark, from Röhm Pharma, Germany), and a composition comprising diltiazem hydrochloride, an organic acid and a lubricant to form multi coating layers.
  • a sustained release pharmaceutical preparation (see japanese Unexamined Patent Publication No. 193913/1985) in which a core containing a medicinal active ingredient and an organic acid is spray-coated with an ethanol solution of an acrylic polymer having trimethylammoniumethyl group.
  • An object of this invention is to provide a controlled release pharmaceutical preparation giving a so-called sigmoid type dissolution pattern wherein a lag time until the starting of the dissolution of a medicinal compound and the rate of the following dissolution can be controlled and the rate of the dissolution of the medicinal compound does not depend on the pH of a medium for the dissolution.
  • the present invention provides a controlled release pharmaceutical preparation comprising a core containing a medicinal compound and a coating layer containing a water-repellent salt and a water-insoluble and slightly water-permeable acrylic polymer having trimethylammoniumethyl group.
  • Fig. 1 is a graph showing the result of the dissolution test with water as to various controlled release granules (a) to (e) obtained in Test Example 1 which differ from each other in the amount of coating layer.
  • Fig. 2 is a graph showing the result of the dissolution test with water, first fluid and second fluid as to the controlled release granule (d) obtained in Test Example 1.
  • Fig. 3 is a graph showing the change in blood concentration of a medicinal compound in case that the granule (d) was administered to dogs in Test Example 2.
  • Fig. 4 is a graph showing the result of the dissolution test as to a capsule containing various controlled release granules obtained in Test Example 3 which differ from each other in the amount of the coating layer.
  • the controlled release pharmaceutical preparation of the present invention comprises a core containing a medicinal compound and a coating layer containing a water-repellent salt and a water-insoluble and slightly water-permeable acrylic polymer having trimethylammoniumethyl group, which surrounds said core.
  • a coating layer containing a water-repellent salt and a water-insoluble and slightly water-permeable acrylic polymer having trimethylammoniumethyl group, which surrounds said core.
  • another coating layer of at least one material selected from the group consisting of ethylcellulose, hydroxypropylcellulose and a medicinal compound may be provided around said coating layer in the controlled release pharmaceutical preparation of the present invention.
  • a polymer of acrylic acid, methyl acrylate, ethyl acrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate or the like, which has trimethylammoniumethyl group in the molecule may be used as a water-insoluble and slightly water-permeable acrylic polymer constituting the coating layer.
  • a copolymer of ethyl acrylate, methyl methacrylate and ⁇ -acryloyloxyethyltrimethylammonium chloride in which about 0.025 to about 0.033 mole of ⁇ -acryloyloxyethyltrimethylammonium chloride is contained per mole of the other neutral acrylic monomers is preferably used.
  • Such copolymer is, for example, commercially available under trade mark "Eudragit RS" from Röhm Pharma, Germany or the like.
  • the above-mentioned polymer may contain, for instance, a small quantity of a water-permeable polymer.
  • a water-permeable polymer is, for example, commercially available under trade mark "Eudragit RL” from Röhm Pharma, Germany or the like.
  • ethylcellulose or hydroxypropylcellulose which is a material of another coating layer provided around the coating layer of an acrylic polymer, for instance, ethylcellulose containing about 46.5 to about 51.0 % of ethoxy group, hydroxypropylcellulose containing about 53.4 to about 77.5 % of hydroxypropoxy group or the like can be suitably used.
  • a water-repellent salt which constitute the coating layer with an acrylic polymer a salt of higher fatty acid and an alkaline earth metal is preferably used.
  • the salts are calcium stearate, magnecium stearate and the like.
  • the ratio of the above-mentioned acrylic polymer and the water-repellent salt in the coating layer it is adequate that about 0.5 to about 5 parts by weight, preferably about 1.5 to about 4.5 parts by weight and more preferably about 2 to about 4 parts by weight of the acrylic polymer is contained per part by weight of the water-repellent salt.
  • the amount of the coating layer for the core is variable a little depending on the form or the size of the core. However, it is preferable that the amount of the coating layer to be used tends to increase a bit depending on the increase of the surface area per unit weight, that is, the decrease of the particle size of the core. For example, in case of spherical particles having mean particle size of about 500 to about 1000 ⁇ m, the amount of the coating layer is about 5 to about 80 %, preferably about 7 to about 50 %, in particular, preferably about 8 to about 30 %, based on the weight of the core.
  • the form of the core to be coated is not particularly limited and various forms such as plain tablet, pill, granule and fine granule may be suitably used.
  • the granulated cores having mean particle size of about 300 to about 5000 ⁇ m, in particular, about 500 to about 1500 ⁇ m may be preferably used.
  • the medicinal compound to be contained in the core is not particularly limited.
  • calcium antagonists such as diltiazem hydrochloride, verapamil hydrochloride, nicardipine, nitrendipine and nimodipine, antiasthmatic agents such as theophylline and trimetaquinol, water soluble vitamins, antibiotics, antimalignatumor agents, antipyretic analgesics, antihyperglycemic agents and the like may be used.
  • additives such as an excipient, a binder, a lubricant, an aggregation-preventing agent and a solubilizer for a medicinal compound which are usually used in this field may be contained in the core.
  • excipients are sugars such as sucrose, lactose, mannitol and glucose, starch, crystalline cellulose, calcium phosphate, calcium sulfate, calcium lactate and the like.
  • carriers for regulating particle sizes are sucrose, lactose, starch, crystalline cellulose and the like.
  • binders are polyvinylalcohol, polyacrylic acid, polymethacrylic acid, polyvinylpyrrolidone, glucose, sucrose, lactose, maltose, sorbitol, mannitol, hydroxyethylcellulose, hydroxypropylmethylcellulose, hydroxypropylcellulose, macrogols, arabic gum, gelatin, agar, starch and the like.
  • lubricants are stearic acid, talc and the like.
  • aggregation-preventing agents are the above-mentioned lubricants, silicone dioxide, colloidal silicone dioxide and the like.
  • solubilizers for medicinal compounds are organic acids such as fumaric acid, succinic acid and malic acid and the like.
  • the pharmaceutical preparation of the present invention can be prepared by coating cores containing a medicinal compound with a dispersion of a water-insoluble and slightly water-permeable acrylic polymer having trimethylammoniumethyl group and a water-repellent salt.
  • the preparation of the cores can be carried out according to the usual procedure for the preparation, for example, as described in Lemingtons Pharmaceutical Sciences 17 , 1603-1632, 1633-1643 (Mack Publishing Company, published in 1985).
  • the cores can be prepared by granulating the composition of a medicinal compound, a binder and, as occasion demands, other additives such as an exicipent according to the method of wet oscillating granulation, rotating granulation, fluidizing bed granulation or the like to obtain granules.
  • the cores may be prepared using carriers for regulating particle sizes. That is, spherically granulated carriers may be coated with a medicinal compound according to the usual method such as powder coating method to obtain the cores. Powder coating can be carried out, for instance, by gradually adding a medicinal compound or a mixture of the medicinal compound and suitable additives such as an excipient with spraying a solution obtained by dissolving a binder in a suitable solvent such as water, a lower alcohol such as methanol, ethanol, propanol, isopropanol or butanol, a lower alkanone such as acetone or methylethylketone, chloroform, dichloromethane, dichloroethane or a mixture thereof, on carrier particles to be cores, according to the method of rotating granulation, pan coating, fluidizing bed coating or the like.
  • suitable solvent such as water, a lower alcohol such as methanol, ethanol, propanol, isopropanol or butanol, a lower al
  • the coating for thus obtained cores can be carried out by adhering a dispersion of a water-repellent salt and an acrylic polymer to the cores followed by drying.
  • a dispersion medium for the above-mentioned component of the coating layer water, an alcohol such as methanol, ethanol or propanol, a ketone such as acetone, a halogenated hydrocarbon such as methylenechloride or chloroform, a mixture thereof or the like is exemplified.
  • Water, an alcohol or a mixture thereof is preferable, and ethanol or a mixture of ethanol and water is particularly preferable.
  • the coating can be carried out according to a method generally used in the art for preparation such as the method of fluidizing bed coating or pan coating.
  • the coating can be carried out as follows. That is, while the cores are fluidized in an apparatus by means of air pressure, they are spray-coated with an aqueous dispersion of a water-repellent salt and an acrylic acid polymer at an adequate rate from the nozzle of the spray-gun.
  • the concentration of a water-repellent salt and an acrylic polymer in the dispersion is not particularly limited, but it is preferable that these components are added within the above-mentioned scope of the preferable proportion of both components, to be the concentration of about 5 to about 40 % by weight.
  • a plasticizer, a coloring agent and the like may be contained in the dispersion.
  • a plasticizer for instance, triacetin, triethyl citrate, acetyltributyl citrate, diethyl phthalate, polyethyleneglycol, polysorbate or the like can be suitably used.
  • the amount of the plasticizer to be used is preferably about 5 to about 40 % by weight based on the weight of an acrylic polymer.
  • the drying of thus obtained coating layer can be easily carried out, for example, by heating at about 35 to about 100°C, particularly about 40 to about 70°C.
  • the other form of the pharmaceutical preparation of the present invention wherein another coating layer made of at least one material selected from the group consisting of ethylcellulose, hydroxypropylcellulose and a medicinal compound is provided around the coating layer containing a water-repellent salt and a water-insoluble and slightly water-permeable acrylic polymer having trimethylammoniumethyl group, can be easily prepared by further coating the above-mentioned pharmaceutical preparation having the coating layer of an acrylic polymer with these components according to the usual method.
  • the solution prepared by dissolving ethylcellulose or hydroxypropylcellulose in water, methanol, ethanol, acetone or a mixed solvent thereof to be the concentration of about 0.5 to about 10 % may be sprayed for coating.
  • the solution or dispersion containing said medicinal compound or a mixture of the medicinal compound and suitable additives such as an excipient and a binder may be sprayed for coating according to the usual method.
  • the additives for instance, the above-mentioned binders and excipients may be suitably used.
  • controlled release pharmaceutical preparation of the present invention may be administered as it is or in a form filled in capsules.
  • the pharmaceutical preparation of the present invention has the following characteristics because of its coating layer of a slightly water-permeable acrylic polymer. That is, a medicinal active ingredient rapidly dissolves from the preparation after a certain period which depends upon the amount of the coating layer although it never dissolves after administration until the certain time passes. Besides, the time until the start of the dissolution of a medicinal active ingredient is optionally adjustable by changing the amount of the coating layer.
  • the pharmaceutical preparation of the present invention is useful as a pharmaceutical preparation wherein the starting of the dissolution of a pharmaceutical compound can be adjusted by itself. And it is further useful that the pharmaceutical preparation which can retain an effective blood concentration for many hours can be obtained by combining various pharmaceutical preparations which differ from each other in the amount of the coating layer or in a kind of a component of the coating layer, according to the present invention.
  • the pharmaceutical preparation of the present invention wherein the coating layer of a slightly water-permeable acrylic polymer is futher coated with ethylcellulose, hydroxypropylcellulose or the like has a following advantage. That is, because the dissolution rate of a medicinal compound after a lag time in such pharmaceutical preparation is smaller than that in a pharmaceutical preparation whose coating layer of an acrylic polymer and a water-repellent salt is not further coated, the most suitable dissolution pattern can be obtained by employing the above-mentioned coating layer in accordance with a kind of medicinal active ingredient.
  • these pharmaceutical preparations also have an advantage of being useful for preventing the aggregation of the preparations, which occurs during preparing them.
  • the pharmaceutical preparation wherein the layer of a medicinal compound is provided around the coating layer of an acrylic polymer can start the dissolution of the inside medicinal compound when the blood concentration originated in the outside medicinal compound has lowered after its dissolution followed by the rise of its concentration, by adjusting the amounts of the medicinal compound layer and an acrylic polymer layer or providing another coating layer of hydroxypropylcellulose or the like around the layer of a medicinal compound. Therefore, the pharmaceutical preparation of the present invention has an advantage that it can be administered as a pharmaceutical preparation suitable for administration a day.
  • Nonpareil granulated sucrose, from Freund Industrial Co. Ltd., Japan having the diameter of 350 to 500 ⁇ m (80 g) was put into the centrifugal fluidizing type granulating and coating apparatus (CF-360EX Type, made by Freund Industrial Co. Ltd., Japan) and rolled in it.
  • CF-360EX Type centrifugal fluidizing type granulating and coating apparatus
  • this plain granule was spray-coated with a solution containing 30 parts of Eudragit RS, 10 parts of calcium stearate and 3 parts of triethyl citrate to obtain various controlled release pharmaceutical preparations (a) to (e) containing diltiazem hydrochloride, which differ from each other in the amount of the coating layer on the plain granule as shown in Table 1.
  • Plain granule containing diltiazem hydrochloride which was not yet coated was used as a control preparation.
  • Fig. 1 The result of the dissolution test in 1 is shown in Fig. 1. It is recognized that according to the pharmaceutical preparation of the present invention, the medicinal compounds are completely released and their dissolution patterns show sigmoid type in water, although the lag time until the start of the dissolution is prolonged according as the increase of the amount of the coating layer in the pharmaceutical preparation.
  • a medicinal compound dissolves immediately after a lag time irrespective of the pH change in the digestive tract.
  • the controlled release pharmaceutical preparation (d) obtained in Test Example 1 was orally administered (dose: 100 mg as the amount of diltiazem hydrochloride) to dogs. After administration the blood was collected from vein at fixed times. The plasma concentration of diltiazem hydrochloride was measured by high performance liquid chromatography.
  • the controlled release pharmaceutical preparations (a) (373 g) and (d) (800 g) obtained in the Test Example 1 and the plain granule (111 g) containing diltiazem hydrochloride were mixed.
  • the mixture ( 128 mg) containing 100 mg of diltiazem hydrochloride was filled into a gelatin capsule to obtain a controlled release capsule.
  • Nonpareil 103 (granulated sucrose, from Freund Industrial Co. Ltd., Japan) which was a spherically granulated sucrose having the diameter of 350 to 500 ⁇ m (800 g) was put into the centrifugal fluidizing type granulating and coating apparatus (made by Freund Industrial Co. Ltd., Japan hereinafter referred to as CF apparatus) and rolled in it. Thereto was gradually spread fine powder of diltiazem hydrochloride (9 kg) with spraying a solution of polyvinylpyrrolidone (200 g) in a mixture of ethanol and water ( 2 : 3 ) ( 6. 4 kg).
  • Example 2 The procedure was carried out in the same manner as in Example 1 except that a mixture of Eudragit RS (112 g), calcium stearate (37 g), triethyl citrate (11 g), ethanol (210 g) and water (430 g) was used as a coating solution to obtain a controlled release pharmaceutical preparation containing diltiazem hydrochloride (yield: 1.16 kg).
  • Example 2 The procedure was carried out in the same manner as in Example 1 except that a mixture of Eudragit RS (140 g), calcium stearate (47 g), triethyl citrate (14 g), ethanol (267 g) and water (533 g) was used as a coating solution to obtain a controlled release pharmaceutical preparation containing diltiazem hydrochloride (yield: 1.2 kg).
  • Example 3 The procedure was carried out in the same manner as in Example 3 except that magnesium stearate (47 g) was used instead of calcium stearate to obtain a controlled release pharmaceutical preparation containing diltiazem hydrochloride (yield: 1.2 kg).
  • the controlled release pharmaceutical preparation (0.56 kg) containing diltiazem hydrochloride obtained in the same manner as in Example 3 was put into CF apparatus and spray-coated with a coating solution consisting of ethylcellulose (9.5 g), hydroxypropylcellulose (0.5 g), ethanol (59 g) and water (32 g). Then the preparation was dried at 60°C for 16 hours to obtain a controlled release pharmaceutical preparation containing diltiazem hydrochloride (yield: 0.57 kg).
  • the controlled release pharmaceutical preparation (1.12 kg) containing diltiazem hydrochloride obtained in the same manner as in Example 3 was put into CF apparatus and spray-coated with a coating solution consisting of diltiazem hydrochloride (151 g), polyvinylpyrrolidone (12 g), ethanol (87 g) and water (203 g). Then the preparation was dried at 60°C for 16 hows to obtain a controlled release pharmaceutical preparation containing diltiazem hydrochloride, wherein the part which rapidly released diltiazem hydrochloride was provided in its surface layer.
  • Nonpareil 103 which was a spherically granulated sucrose having the diameter of 350 to 500 ⁇ m (1500 g) was put into CF apparatus and rolled in it. Thereto was gradually spread fine powder of nicotinamide (NA) (900 g) with spraying a solution of sucrose (135 g) in a mixture (465 g) of ethanol and water (1:3). The plain granule having the diameter of 12 to 20 mesh (1400 to 840 ⁇ m) containing NA, wherein Nonpareil was coated around its surface with NA, was thus prepared.
  • NA nicotinamide
  • the obtained plain granule (0.5 kg) containing NA was put into CF apparatus and spray-coated with a solution consisiting of Eudragit RS (105 g), calcium stearate (35 g), triethyl citrate (11 g), ethanol (200 g) and water (400 g). Then the granule was dried by heating at 60°C for 16 hours to obtain a controlled release pharmaceutical preparation containing NA (yield: 0.56 kg).
  • Nonpareil 103 which was a spherically granulated sucrose having the diameter of 500 to 710 ⁇ m (1.04 kg) was put into CF apparatus and rolled in it. Thereto was gradually spread a mixed powder of fine powder of (+)-( 2S, 3S)-3-acetoxy-8-chloro-5-[2-(dimethylamino)ethyl]-2, 3-dihydro-2-(4-methoxyphenyl)- 1,5-benzothiazepin-4(5H)-one ⁇ maleate (hereinafter referred to as Clentiazem) (1.176 kg) and succinic acid (1.96 kg) with spraying a solution of sucrose (0.78 kg) in the mixture of ethanol and water (1 : 3) (2.22 kg).
  • Clentiazem (1.176 kg
  • succinic acid (1.96 kg
EP91305834A 1990-06-28 1991-06-27 Préparation pharmaceutique à libération contrÔlée Expired - Lifetime EP0463877B2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP171762/90 1990-06-28
JP17176290 1990-06-28
SG4995A SG4995G (en) 1990-06-28 1995-01-13 Controlled release pharmaceutical preparation

Publications (3)

Publication Number Publication Date
EP0463877A1 true EP0463877A1 (fr) 1992-01-02
EP0463877B1 EP0463877B1 (fr) 1994-06-01
EP0463877B2 EP0463877B2 (fr) 1997-07-02

Family

ID=26494375

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91305834A Expired - Lifetime EP0463877B2 (fr) 1990-06-28 1991-06-27 Préparation pharmaceutique à libération contrÔlée

Country Status (17)

Country Link
US (1) US5137733A (fr)
EP (1) EP0463877B2 (fr)
JP (1) JP2558396B2 (fr)
KR (1) KR0133511B1 (fr)
CN (1) CN1040061C (fr)
AT (1) ATE106241T1 (fr)
CA (1) CA2045358C (fr)
DE (1) DE69102211T3 (fr)
DK (1) DK0463877T3 (fr)
ES (1) ES2055962T5 (fr)
FI (1) FI103476B1 (fr)
GR (1) GR3024471T3 (fr)
HK (1) HK33895A (fr)
HU (1) HU214590B (fr)
IE (1) IE64629B1 (fr)
IL (1) IL98611A (fr)
SG (1) SG4995G (fr)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0553392A1 (fr) * 1992-01-27 1993-08-04 Euro-Celtique S.A. Formulations stabilisées à libération contrôlée enrobées d'une couche de polymère acrylique
EP0636366A2 (fr) * 1993-07-27 1995-02-01 Euroceltique S.A. Formulations à libérations contrôlée enrobée d'une dispersion aqueuse de polymères acryliques
US5830503A (en) * 1996-06-21 1998-11-03 Andrx Pharmaceuticals, Inc. Enteric coated diltiazem once-a-day formulation
US5834023A (en) * 1995-03-24 1998-11-10 Andrx Pharmaceuticals, Inc. Diltiazem controlled release formulation
WO1999059557A1 (fr) * 1998-05-20 1999-11-25 Laboratoires Prographarm Forme pharmaceutique multiparticulaire a liberation programmee et pulsee et son procede de preparation
US6039979A (en) * 1999-01-13 2000-03-21 Laboratoires Prographarm Multiparticulate pharmaceutical form with programmed and pulsed release and process for its preparation
WO2000042998A1 (fr) * 1999-01-21 2000-07-27 Elan Corporation, Plc Formulation de bisoprolol multiparticulaire
US6129933A (en) * 1991-12-24 2000-10-10 Purdue Pharma Lp Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer
WO2001047500A1 (fr) * 1999-12-23 2001-07-05 Pfizer Products Inc. Forme de dosage de medicament entraine par un hydrogel
US6306438B1 (en) 1997-07-02 2001-10-23 Euro-Celtique, S.A. Stabilized sustained release tramadol formulations
WO2002028376A3 (fr) * 2000-10-03 2003-03-06 Mehta Atul M Preparations a chrono-administration et methode d'utilisation
WO2003041696A1 (fr) * 2001-11-15 2003-05-22 Athpharma Procedes et compositions d'utilisation de (s)-bisoprolol
US6733789B1 (en) 1999-01-21 2004-05-11 Biovail Laboratories, Inc. Multiparticulate bisoprolol formulation
EP1419766A1 (fr) * 1993-06-23 2004-05-19 Euro-Celtique S.A. Formulations à libération controlée enrobées avec dispersions aqueuses d'éthylcellulose
US6984402B2 (en) 2000-10-03 2006-01-10 Elite Laboratories, Inc. Chrono delivery formulations and method of treating atrial fibrillation
US7070806B2 (en) 1992-01-27 2006-07-04 Purdue Pharma Lp Controlled release formulations coated with aqueous dispersions of acrylic polymers
US8026286B2 (en) 1999-12-23 2011-09-27 Bend Research, Inc. Pharmaceutical compositions providing enhanced drug concentrations
EP2386295A2 (fr) 2004-09-10 2011-11-16 Jagotec Ag Comprimes a liberation gastro-intestinale du principe actif regulee en foction du temps et du site
US8168218B2 (en) 2003-04-24 2012-05-01 Jagotec Ag Delayed release tablet with defined core geometry
US9974752B2 (en) 2014-10-31 2018-05-22 Purdue Pharma Methods and compositions particularly for treatment of attention deficit disorder
US10722473B2 (en) 2018-11-19 2020-07-28 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1053808C (zh) * 1993-04-24 2000-06-28 章修纲 尼非地平控释剂型
JP2916978B2 (ja) * 1993-08-25 1999-07-05 エスエス製薬株式会社 放出開始制御型製剤
US5834024A (en) * 1995-01-05 1998-11-10 Fh Faulding & Co. Limited Controlled absorption diltiazem pharmaceutical formulation
US5922736A (en) * 1995-12-04 1999-07-13 Celegene Corporation Chronic, bolus administration of D-threo methylphenidate
US5837284A (en) * 1995-12-04 1998-11-17 Mehta; Atul M. Delivery of multiple doses of medications
US6486177B2 (en) * 1995-12-04 2002-11-26 Celgene Corporation Methods for treatment of cognitive and menopausal disorders with D-threo methylphenidate
US8071128B2 (en) 1996-06-14 2011-12-06 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US6962997B1 (en) * 1997-05-22 2005-11-08 Celgene Corporation Process and intermediates for resolving piperidyl acetamide steroisomers
CN1296417A (zh) 1998-02-10 2001-05-23 卫福有限公司 控释制剂
US6524620B2 (en) 1998-07-20 2003-02-25 Andrx Pharmaceuticals, Inc. Diltiazem controlled release formulation and method of manufacture
DE19845358A1 (de) * 1998-10-02 2000-04-06 Roehm Gmbh Überzogene Arzneiformen mit kontrollierter Wirkstoffabgabe
US20010055613A1 (en) 1998-10-21 2001-12-27 Beth A. Burnside Oral pulsed dose drug delivery system
US6270805B1 (en) 1998-11-06 2001-08-07 Andrx Pharmaceuticals, Inc. Two pellet controlled release formulation for water soluble drugs which contains an alkaline metal stearate
US20040185099A1 (en) * 2000-01-20 2004-09-23 Biovail Laboratories, Inc. Multiparticulate bisoprolol formulation
US6635277B2 (en) 2000-04-12 2003-10-21 Wockhardt Limited Composition for pulsatile delivery of diltiazem and process of manufacture
SE0100200D0 (sv) 2001-01-24 2001-01-24 Astrazeneca Ab New film coating
WO2002094172A2 (fr) * 2001-05-22 2002-11-28 Euro-Celtique Forme posologique compartimentee
US9358214B2 (en) 2001-10-04 2016-06-07 Adare Pharmaceuticals, Inc. Timed, sustained release systems for propranolol
US20030118652A1 (en) * 2001-11-15 2003-06-26 John Kelly Methods and compositions for use of (S)-bisoprolol
US6663888B2 (en) * 2001-12-14 2003-12-16 Eurand Pharmaceuticals Ltd. Pulsatile release histamine H2 antagonist dosage form
US20050025824A1 (en) * 2001-12-14 2005-02-03 Eurand Pharmaceuticals Ltd. Pulsatile release histamine H2 antagonist dosage form
US8367111B2 (en) * 2002-12-31 2013-02-05 Aptalis Pharmatech, Inc. Extended release dosage forms of propranolol hydrochloride
CA2518806C (fr) * 2003-03-11 2012-05-01 Seikagaku Corporation Composition polysaccharide photoreticulee et procede de fabrication
FR2861990B1 (fr) * 2003-11-10 2006-02-10 Nouveaux Produits Pharma Comprimes faiblement doses a reseau de polymeres
US20050239830A1 (en) * 2004-04-26 2005-10-27 Vikram Khetani Methods of diminishing co-abuse potential
EP1759719B1 (fr) * 2004-05-07 2015-01-07 Seikagaku Corporation Matière de remplissage de nucleus pulposus
US8747895B2 (en) 2004-09-13 2014-06-10 Aptalis Pharmatech, Inc. Orally disintegrating tablets of atomoxetine
US9884014B2 (en) 2004-10-12 2018-02-06 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
NZ589750A (en) 2004-10-21 2012-07-27 Aptalis Pharmatech Inc Taste-masked pharmaceutical compositions with gastrosoluble pore-formers
JP2008523097A (ja) * 2004-12-09 2008-07-03 セルジーン・コーポレーション Ｄ−トレオメチルフェニデートを用いた治療
US9161918B2 (en) 2005-05-02 2015-10-20 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US8846100B2 (en) * 2006-05-12 2014-09-30 Shire Llc Controlled dose drug delivery system
CA2655682A1 (fr) 2006-08-03 2008-02-07 Nitec Pharma Ag Traitement glucocorticoidique a liberation retardee de maladie rhumatoide
JP2008024708A (ja) * 2007-08-20 2008-02-07 Euro-Celtique Sa アクリル系ポリマーの水性分散液で被膜した放出制御型製剤及びその方法
PL2358360T3 (pl) * 2008-11-18 2017-02-28 Ucb Biopharma Sprl Preparaty o przedłużonym uwalnianiu zawierające pochodną 2-okso-1-pirolidyny
CN101904813A (zh) * 2009-04-22 2010-12-08 苏维拉克皮肤及健康护理公司 冻干包衣的模制品
NZ600256A (en) 2009-12-02 2014-05-30 Aptalis Pharma Ltd Fexofenadine microcapsules and compositions containing them
WO2012074042A1 (fr) * 2010-12-03 2012-06-07 日本曹達株式会社 Hydroxyalkylcellulose
US9603809B2 (en) 2011-03-23 2017-03-28 Ironshore Pharmaceuticals & Development, Inc. Methods of treatment of attention deficit hyperactivity disorder
US10905652B2 (en) 2011-03-23 2021-02-02 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US11241391B2 (en) 2011-03-23 2022-02-08 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US9283214B2 (en) 2011-03-23 2016-03-15 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US8927010B2 (en) 2011-03-23 2015-01-06 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US8916588B2 (en) 2011-03-23 2014-12-23 Ironshore Pharmaceuticals & Development, Inc. Methods for treatment of attention deficit hyperactivity disorder
EP4011364B1 (fr) 2011-03-23 2023-12-13 Ironshore Pharmaceuticals & Development, Inc. Procédés et compositions pour le traitement de troubles du déficit de l'attention
US10292937B2 (en) 2011-03-23 2019-05-21 Ironshore Pharmaceuticals & Development, Inc. Methods of treatment of attention deficit hyperactivity disorder
US9119809B2 (en) 2011-03-23 2015-09-01 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US9498447B2 (en) 2011-03-23 2016-11-22 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
JP5146859B2 (ja) * 2011-07-11 2013-02-20 ユーロ−セルティーク エス．エイ． アクリル系ポリマーの水性分散液で被膜した放出制御型製剤及びその方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0315414A1 (fr) * 1987-11-06 1989-05-10 Tanabe Seiyaku Co., Ltd. Dispositif pharmaceutique à libération contrôlée
EP0386440A1 (fr) * 1989-02-11 1990-09-12 Bayer Ag Médicament à libération contrôlée

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5944311A (ja) * 1982-09-07 1984-03-12 Santen Pharmaceut Co Ltd 徐放性顆粒およびその製造法
IE56999B1 (en) * 1983-12-22 1992-03-11 Elan Corp Plc Pharmaceutical formulation
US5002776A (en) * 1983-12-22 1991-03-26 Elan Corporation, Plc Controlled absorption diltiazem formulations
US4559225A (en) * 1984-02-16 1985-12-17 Fourman Robert G Sunscreen composition
JPH0621066B2 (ja) * 1984-03-14 1994-03-23 杏林製薬株式会社 ３―イソブチリル―２―イソプロピルピラゾロ〔１，５―ａ〕ピリジンの徐放性医薬品組成物
GB8518301D0 (en) * 1985-07-19 1985-08-29 Fujisawa Pharmaceutical Co Hydrodynamically explosive systems
GB8707416D0 (en) * 1987-03-27 1987-04-29 Wellcome Found Pharmaceutical formulations
US4983401A (en) * 1989-05-22 1991-01-08 Kinaform Technology, Inc. Sustained release pharmaceutical preparations having pH controlled membrane coatings
US5013557A (en) * 1989-10-03 1991-05-07 Warner-Lambert Company Taste masking compositions comprising spray dried microcapsules containing sucralfate and methods for preparing same
JPH0674206B2 (ja) * 1989-12-28 1994-09-21 田辺製薬株式会社 放出制御型製剤およびその製法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0315414A1 (fr) * 1987-11-06 1989-05-10 Tanabe Seiyaku Co., Ltd. Dispositif pharmaceutique à libération contrôlée
EP0386440A1 (fr) * 1989-02-11 1990-09-12 Bayer Ag Médicament à libération contrôlée

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6129933A (en) * 1991-12-24 2000-10-10 Purdue Pharma Lp Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer
US7316821B2 (en) 1991-12-24 2008-01-08 Purdue Pharma, L.P. Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer
US6905709B2 (en) 1991-12-24 2005-06-14 Purdue Pharma, Lp Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer
US7070806B2 (en) 1992-01-27 2006-07-04 Purdue Pharma Lp Controlled release formulations coated with aqueous dispersions of acrylic polymers
EP0553392A1 (fr) * 1992-01-27 1993-08-04 Euro-Celtique S.A. Formulations stabilisées à libération contrôlée enrobées d'une couche de polymère acrylique
US5580578A (en) * 1992-01-27 1996-12-03 Euro-Celtique, S.A. Controlled release formulations coated with aqueous dispersions of acrylic polymers
US5639476A (en) * 1992-01-27 1997-06-17 Euro-Celtique, S.A. Controlled release formulations coated with aqueous dispersions of acrylic polymers
US6143353A (en) * 1992-01-27 2000-11-07 Purdue Pharma Lp Controlled release formulations coated with aqueous dispersions of acrylic polymers
EP1419766A1 (fr) * 1993-06-23 2004-05-19 Euro-Celtique S.A. Formulations à libération controlée enrobées avec dispersions aqueuses d'éthylcellulose
EP0636366A3 (fr) * 1993-07-27 1998-02-04 Euroceltique S.A. Formulations à libérations contrôlée enrobée d'une dispersion aqueuse de polymères acryliques
EP0636366A2 (fr) * 1993-07-27 1995-02-01 Euroceltique S.A. Formulations à libérations contrôlée enrobée d'une dispersion aqueuse de polymères acryliques
US5834023A (en) * 1995-03-24 1998-11-10 Andrx Pharmaceuticals, Inc. Diltiazem controlled release formulation
US5830503A (en) * 1996-06-21 1998-11-03 Andrx Pharmaceuticals, Inc. Enteric coated diltiazem once-a-day formulation
US6306438B1 (en) 1997-07-02 2001-10-23 Euro-Celtique, S.A. Stabilized sustained release tramadol formulations
US6645527B2 (en) 1997-07-02 2003-11-11 Euro-Celtique S.A. Stabilized sustained release tramadol formulations
FR2778848A1 (fr) * 1998-05-20 1999-11-26 Prographarm Lab Forme pharmaceutique multiparticulaire a liberation programmee et pulsee et son procede de preparation
WO1999059557A1 (fr) * 1998-05-20 1999-11-25 Laboratoires Prographarm Forme pharmaceutique multiparticulaire a liberation programmee et pulsee et son procede de preparation
US6039979A (en) * 1999-01-13 2000-03-21 Laboratoires Prographarm Multiparticulate pharmaceutical form with programmed and pulsed release and process for its preparation
WO2000042998A1 (fr) * 1999-01-21 2000-07-27 Elan Corporation, Plc Formulation de bisoprolol multiparticulaire
US6733789B1 (en) 1999-01-21 2004-05-11 Biovail Laboratories, Inc. Multiparticulate bisoprolol formulation
WO2001047500A1 (fr) * 1999-12-23 2001-07-05 Pfizer Products Inc. Forme de dosage de medicament entraine par un hydrogel
US8026286B2 (en) 1999-12-23 2011-09-27 Bend Research, Inc. Pharmaceutical compositions providing enhanced drug concentrations
EP1967185A1 (fr) * 1999-12-23 2008-09-10 Pfizer Products Inc. Forme de dosage de médicament entraîné par un hydrogél
WO2002028376A3 (fr) * 2000-10-03 2003-03-06 Mehta Atul M Preparations a chrono-administration et methode d'utilisation
US6984402B2 (en) 2000-10-03 2006-01-10 Elite Laboratories, Inc. Chrono delivery formulations and method of treating atrial fibrillation
WO2003041696A1 (fr) * 2001-11-15 2003-05-22 Athpharma Procedes et compositions d'utilisation de (s)-bisoprolol
US9040085B2 (en) 2003-04-24 2015-05-26 Jagotec Ag Delayed release tablet with defined core geometry
US8168218B2 (en) 2003-04-24 2012-05-01 Jagotec Ag Delayed release tablet with defined core geometry
US8309124B2 (en) 2003-04-24 2012-11-13 Jagotec Ag Delayed release tablet with defined core geometry
US8394407B2 (en) 2003-04-24 2013-03-12 Jagotec Ag Delayed release tablet with defined core geometry
US9186332B2 (en) 2003-04-24 2015-11-17 Jagotec Ag Delayed release tablet with defined core geometry
US9884021B2 (en) 2003-04-24 2018-02-06 Jagotec Ag Delayed release tablet with defined core geometry
EP2386295A2 (fr) 2004-09-10 2011-11-16 Jagotec Ag Comprimes a liberation gastro-intestinale du principe actif regulee en foction du temps et du site
US10292939B2 (en) 2014-10-31 2019-05-21 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10111839B2 (en) 2014-10-31 2018-10-30 Purdue Pharma Methods and compositions particularly for treatment of attention deficit disorder
US9974752B2 (en) 2014-10-31 2018-05-22 Purdue Pharma Methods and compositions particularly for treatment of attention deficit disorder
US10292938B2 (en) 2014-10-31 2019-05-21 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10449159B2 (en) 2014-10-31 2019-10-22 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10500162B2 (en) 2014-10-31 2019-12-10 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10507186B2 (en) 2014-10-31 2019-12-17 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10512612B2 (en) 2014-10-31 2019-12-24 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10512613B2 (en) 2014-10-31 2019-12-24 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10568841B2 (en) 2014-10-31 2020-02-25 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10688060B2 (en) 2014-10-31 2020-06-23 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US11896722B2 (en) 2014-10-31 2024-02-13 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
US10722473B2 (en) 2018-11-19 2020-07-28 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder

Also Published As

Publication number Publication date
CN1040061C (zh) 1998-10-07
DE69102211T2 (de) 1994-09-15
DE69102211T3 (de) 1997-08-28
EP0463877B2 (fr) 1997-07-02
US5137733A (en) 1992-08-11
IE64629B1 (en) 1995-08-23
HU912170D0 (en) 1991-12-30
IE912166A1 (en) 1992-01-01
ES2055962T5 (es) 1997-09-16
FI912952A0 (fi) 1991-06-18
GR3024471T3 (en) 1997-11-28
HK33895A (en) 1995-03-17
KR0133511B1 (ko) 1998-04-23
AU634400B2 (en) 1993-02-18
IL98611A0 (en) 1992-07-15
KR920000313A (ko) 1992-01-29
ES2055962T3 (es) 1994-09-01
AU7924391A (en) 1992-01-02
JPH04235123A (ja) 1992-08-24
FI103476B (fi) 1999-07-15
DE69102211D1 (de) 1994-07-07
ATE106241T1 (de) 1994-06-15
CA2045358C (fr) 1998-04-28
HUT59321A (en) 1992-05-28
IL98611A (en) 1998-10-30
SG4995G (en) 1995-06-16
FI912952A (fi) 1991-12-29
CN1058533A (zh) 1992-02-12
EP0463877B1 (fr) 1994-06-01
HU214590B (hu) 1998-04-28
JP2558396B2 (ja) 1996-11-27
DK0463877T3 (da) 1994-06-27
FI103476B1 (fi) 1999-07-15
CA2045358A1 (fr) 1991-12-29

Similar Documents

Publication Publication Date Title
EP0463877B1 (fr) Préparation pharmaceutique à libération contrôlée
EP0253684B1 (fr) Préparation à libération prolongée et sa fabrication
EP0640337B1 (fr) Composition pharmaceutique avec commencement et vitesse contrôlés de la libération
EP0149920B1 (fr) Formulation pharmaceutique
US5601845A (en) Pharmaceutical spheroid formulation
AU772168B2 (en) Timed pulsatile drug delivery systems
KR940002655B1 (ko) 조절 방출성 용량 형태
EP0605174B1 (fr) Préparation pharmaceutique à libération retardée et continue
FI103475B (fi) Menetelmä kontrolloidusti vapauttavan valmisteen valmistamiseksi
CA1339078C (fr) Preparation pharmaceutique a liberation-retard; methode de preparation
JP3426230B2 (ja) 複数層の制御放出処方剤
EP0142561A1 (fr) Preparation a base de nifedipine a action prolongee
EP0386967B1 (fr) Matériau d'enrobage contrôlant la libération d'un médicament pour des formulations à activité prolongée
JPH07552B2 (ja) 持効性製剤
US5258186A (en) Drug release controlling coating material for long acting formulations
JPH04338323A (ja) 放出制御製剤およびその製造法
JPH10120571A (ja) 塩酸ジルチアゼム徐放性製剤

Legal Events

Date Code Title Description
REG Reference to a national code

Ref country code: DK

Ref legal event code: T4

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

17P Request for examination filed

Effective date: 19920120

17Q First examination report despatched

Effective date: 19921120

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

REF Corresponds to:

Ref document number: 106241

Country of ref document: AT

Date of ref document: 19940615

Kind code of ref document: T

ITF It: translation for a ep patent filed

Owner name: JACOBACCI CASETTA & PERANI S.P.A.

REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

ET Fr: translation filed
REF Corresponds to:

Ref document number: 69102211

Country of ref document: DE

Date of ref document: 19940707

EPTA Lu: last paid annual fee
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2055962

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3012582

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

EAL Se: european patent in force in sweden

Ref document number: 91305834.3

26 Opposition filed

Opponent name: ROEHM GMBH

Effective date: 19941208

NLR1 Nl: opposition has been filed with the epo

Opponent name: ROHM GMBH

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PUAH Patent maintained in amended form

Free format text: ORIGINAL CODE: 0009272

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: PATENT MAINTAINED AS AMENDED

27A Patent maintained in amended form

Effective date: 19970702

AK Designated contracting states

Kind code of ref document: B2

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

REG Reference to a national code

Ref country code: DK

Ref legal event code: T4

REG Reference to a national code

Ref country code: CH

Ref legal event code: AEN

Free format text: AUFRECHTERHALTUNG DES PATENTES IN GEAENDERTER FORM

NLR2 Nl: decision of opposition
ET3 Fr: translation filed ** decision concerning opposition
REG Reference to a national code

Ref country code: ES

Ref legal event code: DC2A

Kind code of ref document: T5

Effective date: 19970722

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3024471

NLR3 Nl: receipt of modified translations in the netherlands language after an opposition procedure
REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20100709

Year of fee payment: 20

Ref country code: DK

Payment date: 20100610

Year of fee payment: 20

Ref country code: LU

Payment date: 20100616

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 20100610

Year of fee payment: 20

Ref country code: IT

Payment date: 20100622

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20100616

Year of fee payment: 20

Ref country code: ES

Payment date: 20100630

Year of fee payment: 20

Ref country code: CH

Payment date: 20100614

Year of fee payment: 20

Ref country code: BE

Payment date: 20100518

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20100609

Year of fee payment: 20

Ref country code: DE

Payment date: 20100625

Year of fee payment: 20

Ref country code: GB

Payment date: 20100623

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GR

Payment date: 20100519

Year of fee payment: 20

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69102211

Country of ref document: DE

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69102211

Country of ref document: DE

BE20 Be: patent expired

Owner name: *TANABE SEIYAKU CO. LTD

Effective date: 20110627

REG Reference to a national code

Ref country code: NL

Ref legal event code: V4

Effective date: 20110627

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: DK

Ref legal event code: EUP

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20110626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20110627

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20110626

REG Reference to a national code

Ref country code: SE

Ref legal event code: EUG

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20120220

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20110628

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20110628